Alkaloids from the stems and rhizomes of Sinomenium acutum from the Qinling Mountains, China

Abstract

Thirteen undescribed alkaloids (sinotumines A-M), including five oxoisoaporphine, a benzo[h]quinoline, an aporphine, two protoberberine, two hasubanane, and two proaporphine alkaloids, and 50 known analogues were isolated from the 95% aqueous EtOH extract of the stems and rhizomes of Sinomenium acutum. The structures and absolute configurations of the isolates were elucidated on the basis of comprehensive analysis of 1D and 2D NMR, HRMS, single-crystal X-ray diffraction, and comparison of the experimental and calculated electronic circular dichroism (ECD) data. Sinotumine F, a rare benzo[h]quinoline alkaloid, was speculated as an oxidation product of the oxoisoaporphine alkaloid, and its putative biosynthetic pathway is proposed. Sinotumines L and M are the first samples of proaporphine-based heterodimers coupled with 1-heptanone and coniferol alcohol moiety, respectively. The T-cell suppression and NO inhibition effects of the isolates were evaluated.

Keywords: Alkaloids; Benzo[h]quinolone; NO inhibition; Proaporphine heterodimers; Sinomenium acutum (Thumb.) Rehd. et Wils. Menispermaceae; T-cell suppression.